Category: 885277-48-5

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 885277-48-5, name is Methyl 2-bromo-6-methylnicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-bromo-6-methylnicotinate

To a stirred solution of methyl 2-bromo-6-methylnicotinate (US2010144760, 2.79 g, 12.1 1 mmol) in acetonitrile (50 ml) (degassed by N2 purge separately) was added bis(triphenylphosphine)palladium(II) chloride (1.063 g, 1.514 mmol). The reaction mixture was heated up to 70 C and diisopropyl ethyl amine (7.83 g, 60.6 mmol) was added slowly, followed by a solution of (R)-4-(4-(3-ethynylcyclopent-2- en- l-yl)piperazin- l-yl)benzonitrile (Compound lj, 2.8 g, 10.10 mmol) in acetonitrile (20 ml) was added slowly at the same temperature. The reaction mixture was heated and stirred at 80-85 C for 14 hrs. The progress of the reaction was monitored by TLC. The reaction mixture was distilled under vaccum to dryness to obtain a crude product which was purified by column chromatography over silica gel (100-200 mesh) using 60-80% ethyl acetate in hexane as an eluent to obtain the title product (0.9 gm, 20.90 % yield). iH NMR (400 MHz, CDC13) delta 8.17 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 8.5 Hz, 2H), 7.20 (d, J = 8.2 Hz, 1H), 6.90 – 6.87 (m, 2H), 6.36 (d, J = 2.3 Hz, 1H), 4.08 – 4.03 (m, 1H), 3.96 (s, 3H), 3.40 – 3.35 (m, 4H), 2.75 – 2.67 (m, 6H), 2.64 (s, 3H), 2.13 – 2.09 (m, 1H), 2.03 – 1.95 (m, 1H). MS: m/z 427.24 (M+l).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 885277-48-5, Methyl 2-bromo-6-methylnicotinate.

Reference:
Patent; LUPIN LIMITED; KARCHE, Navnath, Popat; TILEKAR, Ajay, Ramchandra; KURHADE, Sanjay, Pralhad; JADHAV, Ganesh, Rajaram; GUPTA, Nishant, Ramniwasji; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (191 pag.)WO2017/29601; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 885277-48-5, name is Methyl 2-bromo-6-methylnicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-bromo-6-methylnicotinate

To a stirred solution of methyl 2-bromo-6-methylnicotinate (US2010144760, 2.79 g, 12.1 1 mmol) in acetonitrile (50 ml) (degassed by N2 purge separately) was added bis(triphenylphosphine)palladium(II) chloride (1.063 g, 1.514 mmol). The reaction mixture was heated up to 70 C and diisopropyl ethyl amine (7.83 g, 60.6 mmol) was added slowly, followed by a solution of (R)-4-(4-(3-ethynylcyclopent-2- en- l-yl)piperazin- l-yl)benzonitrile (Compound lj, 2.8 g, 10.10 mmol) in acetonitrile (20 ml) was added slowly at the same temperature. The reaction mixture was heated and stirred at 80-85 C for 14 hrs. The progress of the reaction was monitored by TLC. The reaction mixture was distilled under vaccum to dryness to obtain a crude product which was purified by column chromatography over silica gel (100-200 mesh) using 60-80% ethyl acetate in hexane as an eluent to obtain the title product (0.9 gm, 20.90 % yield). iH NMR (400 MHz, CDC13) delta 8.17 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 8.5 Hz, 2H), 7.20 (d, J = 8.2 Hz, 1H), 6.90 – 6.87 (m, 2H), 6.36 (d, J = 2.3 Hz, 1H), 4.08 – 4.03 (m, 1H), 3.96 (s, 3H), 3.40 – 3.35 (m, 4H), 2.75 – 2.67 (m, 6H), 2.64 (s, 3H), 2.13 – 2.09 (m, 1H), 2.03 – 1.95 (m, 1H). MS: m/z 427.24 (M+l).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 885277-48-5, Methyl 2-bromo-6-methylnicotinate.

Reference:
Patent; LUPIN LIMITED; KARCHE, Navnath, Popat; TILEKAR, Ajay, Ramchandra; KURHADE, Sanjay, Pralhad; JADHAV, Ganesh, Rajaram; GUPTA, Nishant, Ramniwasji; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (191 pag.)WO2017/29601; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 885277-48-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.885277-48-5, name is Methyl 2-bromo-6-methylnicotinate, molecular formula is C8H8BrNO2, molecular weight is 230.06, as common compound, the synthetic route is as follows.

Na2C03 (8.43 g, 80 mmol) was added to a solution of methyl 2-bromo-6-methylnicotinate (6.1 g, 26.5 mmol) and methyl acrylate (6.08 mL, 67.1 mmol) in mixture of DMA (16.99 mL, 181 mmol) and toluene (55 mL) at room temperature. Then the reaction mixture was degassed for 15 min. Tri-r olyl phosphine (0.807 g, 2.65 mmol) and allylpalladium chloride dimer (0.4850 g, 1.326 mmol) were added and the reaction mixture was stirred at 115 C in sealed tube for 5 h. Filtered through pad of Celite, and the filtrate was concentrated under reduced pressure. The resultant crude compound was purified by flash column chromatography on 100-200 mesh silica gel using 20% EtO Ac/pet-ether as an eluent to obtained (///-methyl 2-(3-methoxy-3-oxoprop-l- en-l-yl)-6-methylnicotinate (3.30 g, 43.0% yield) as a colorless oil. 1H NMR (400 MHz, CDCE): d 8.53 (dd, /= 1.2, 15.2 Hz, 1H), 8.22 (d, /= 6.8 Hz, 1H), 7.20-7.11 (m, 2H), 3.94 (s, 3H), 3.82 (s, 3H), 2.60 (s, 3H). LCMS (ES) m/z 236.09 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 885277-48-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Anish; CHEUNG, Mui; EIDAM, Hilary Schenck; JOSHI, Hemant; SU, Dai-Shi; (128 pag.)WO2019/149959; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 885277-48-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 885277-48-5, name is Methyl 2-bromo-6-methylnicotinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 2-bromo-6-methyl-3-pyridinecarboxylate D60 (1.15 g) and Pd(Ph3P)4 (0.2 g, 0.173 mmol) in 1,4-Dioxane (10 ml) stirred under nitrogen at room temperature tributyl(ethenyl)stannane (1.74 g, 5.50 mmol) was added neat in one charge. The reaction mixture was stirred at microwave Personal Chemistry at 95 C. for 30 minutes. The solvent was removed to give the crude title compound. Under similar conditions another batch of D60 (100 mg) was processed to give the crude title compound. The two crudes were joined and purified by flash chromatography on silica (80 g column, gradient elution from Cy to Cy/EtOAc 4:6) to afford the title compound D61 (1.0 g). UPLC (Basic GEN_C): rt=0.73 minutes, peak observed: 178 (M+1). C10H11NO2 requires 177. 1H NMR (400 MHz, CDCl3) delta ppm 8.08 (d, 1H), 7.66 (dd, 1H), 7.12 (d, 1H), 6.52 (d, 1H), 5.59 (dd, 1H), 3.93 (s, 3H), 2.63 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885277-48-5, Methyl 2-bromo-6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem